Uncategorized

When I was 24 years old I was living and working in Boston. I had a great job in finance that paid decently and allowed me to use my then-fluency in Spanish, doing Latin American equity research for a Fortune 500 Company. I loved the city and had a large and growing cohort of friends and colleagues. Shortly thereafter I would leave the city, my job and my friends and move to a city where I had no immediate employment prospects.

Fast forward two-and-a-half years. It’s 2003 and I’m living in St. Louis, Missouri with the good fortune of having just worked as the Travel Assistant (Body Man) in the most highly targeted U.S. Senate campaign in the nation. The campaign helped return the Senate to Republican hands and my candidate, whom I had gone grown close to over the course of the campaign, is now a promising freshman Senator. I’d quickly leave a steady job in that Senator’s office to take a short-term job on another campaign.

Now jump ahead to 2014. I’ve spent the last six years of my life running two of America’s largest center-right public policy organizations. I’ve traveled the country, spoken in front of thousands of people and built tremendous relationships with many of the top professionals in my field. I’m well compensated and have thoroughly enjoyed my work. Clearly, it was time to leave those endeavors and start something completely unproven and risky: my own business.

Those are just a few examples of the kinds of calculated risks I’ve taken throughout my 15 years in grassroots politics. Some of the risks paid off. And a few didn’t. But today I find myself the owner of a successful small business that makes me feel fulfilled, both personally and professionally. And I’d never be here today if I had stayed on my original career path at that Fortune 500 company.

Recently a political colleague and friend approached me about a Congressional candidate who was looking for a young operative to be his Campaign Manager. My friend wanted to know if I knew anyone aggressive and philosophically conservative who might be a good fit and, if so, would I pass along some resumes. Now this is exactly the kind of opportunity that I would’ve jumped at in my 20s as an aspiring young pol and I immediately reached out to five friends who I thought should be interested. They’re all Millennials with decent jobs and one by one each of them professed no interest. I was disappointed. But I can’t say that I was surprised.

It struck me that this wasn’t the first instance I’d seen of Millennials being overly cautious professionally. So I mentioned it to some friends and looked around online. It turns out that risk aversion is one of the defining characteristics of the Millennial generation. The Congressional Institute wrote about this phenomenon, explaining:

“Millennials were highly protected in childhood by a fortress of youth safety initiatives, which they took as evidence that they were truly valuable. This protection has translated into risk aversion in their young-adult lives.”

The risks of being risk averse are, to my mind, at least threefold for Millennials. On a personal level, we know that entrepreneurs are both more likely to be risk takers and more likely to economically outperform those who have more orthodox forms of employment. Millennials stand the risk of missing out on both the personal and financial benefits that entrepreneurism brings and that risk-taking makes possible.

The larger corporate risk, however, is to the American economy. If Millennials continue their risk-avoiding ways, it’s natural to conclude they’d have a smaller proportion of entrepreneurs among them. That could be disastrous for America if it came true.

So at the operational level, the obvious question that arises is, exactly what risky career propositions should young people be willing to take? How does one differentiate between a calculated risk while avoiding foolhardy ones? Here are a few lessons I’ve learned along in my career:

Only take career risks that you’re confident will expand your skill set. If you’re disrupting your career without an eye towards making yourself a more valuable employee/team member, you’re already off on the wrong foot.

Relationships, relationships, relationships. Many of Washington’s most successful operatives and strategists return to public service taking lower paid government jobs every 5-10 years. Why? Because relationships drive success. Each of us is only as successful as the contacts and friends we have. This is true in every industry, from carpentry to investment banking.

Don’t obsess over compensation. Bill Walsh, one of the greatest coaches in NFL history, has a great book called “The Score Takes Care of Itself.” The premise is that, if you take minute care of the little things, the big things take care of themselves. So mind the little things, like the above bullet items. You do those and you’ll end up doing just fine financially.

If all of this talk of risk and reward makes you nervous or congenitally uneasy, there’s a very real chance that career-related risk taking isn’t for you. In fact, you’re probably part of the majority of people who can feel personally and professionally fulfilled without putting yourself through those ups and downs. If so, God bless you. I’m certainly not advocating taking risks for the sake of taking risks. But for those of us who literally can’t sleep at night if we don’t believe we’re attempting to maximize our professional outcomes, I hope my perspective is helpful in some small way.

Professional fulfillment for me has come because I trusted myself to assess my abilities and the professional landscape and take calculated risks based upon those assessments. Taking those risks has enriched my life in ways I never could haveforeseen. And it’s made all the difference in the world. The lesson I’ve taken from my experiences in calculated risk taking and that I’d hope the Millennial generation comes to learn soon is this: the real risk in life lies in taking no risks at all.